Since this kind of trade embargo is so lax, it can only be assumed to be formally a part of the foreign policy strategic goal: create sufficient internal backpressure to liberalise the market, that it makes sense for the Cuban government to give in. I wonder if it works?

There is no specific "only apple" in this. So, all the anti-cuban government info is available via VPN from other places, via the local copy wikipedia &c. It would work on Android. There might be "I trust apple more, I trust icloud more to protect my secrecy" or "Less spyware risk" maybe.

At this point, I would think that being part of a combine which collects old apple gear (actually, almost any ICT gear), puts it in a container, and ships to Havana would work fine. I doubt every US government body wants that so you'd be placed in the position of evading ITAR regulations or some equivalent.

You would think that much the same happens in Syria, Libya, Iran, you-name-it: equipment beyond end-of-life in the developed west winds up either in the waste stream or part of a container delivered via various paths into these economies for the value it has, mending other things or being mended itself.